The Captain Curt Show

How a Pilot Bought a $10M Boutique Hotel | The Hotel Investor Playbook

What if you could invest in boutique hotels without running the hotel? In this episode of The Hotel Investor Playbook, host Michael Russell sits down with Curt Marker—private jet captain, real estate investor, and CEO of Captain Capital—to break down how Curt became a co-GP on a $10M, 130-room boutique hotel in the Smoky Mountains without managing staff or daily operations. They walk through the real mechanics of Curt’s role in the deal, including how he raised $1.5M in capital, evaluated operating partners, and helped guide investors through an unexpected 8-month USDA loan delay using consistent, transparent communication. In this episode, they discuss: * How to add value in hotel deals without being the operator * Why most of Curt’s capital came from people he already knew * What to look for when vetting an operating partner * How a loan delay tested the partnership—and investor confidence * Why honest monthly updates matter more than perfect timelines This conversation is a grounded look at hotel investing for professionals who want exposure to hospitality real estate without taking on operational complexity—and a reminder that trust and communication are just as important as the numbers. 🎧 Original Podcast: The Hotel Investor Playbook 🌐 Learn more: https://www.hotelinvestorplaybook.com/ [https://www.hotelinvestorplaybook.com/] Timestamps 02:05 – Curt’s Background: From Pilot to Real Estate Investor 05:06 – Shifting Focus: Family, Charity, and Long-Term Purpose 08:37 – Staying Flexible Across Asset Classes 11:25 – Why Commercial Real Estate Changed the Game 15:20 – Comparing Short-Term Rentals vs Hotels 18:43 – Breaking Down the Boutique Hotel Deal Structure 22:21 – Adding Value Without Managing Daily Operations 26:16 – The USDA Loan Delay and What Went Wrong 29:14 – Communicating Bad News Without Losing Investor Trust 38:01 – Building a Personal Brand That Raises Capital 45:54 – Where Capital Actually Comes From 52:47 – Advice for First-Time Real Estate Investors CONNECT WITH MICHAEL RUSSELL: Instagram: https://www.instagram.com/reachmichael [https://www.instagram.com/reachmichael] Website: https://www.malama-capital.com/ [https://www.instagram.com/reachmichael] CONNECT WITH US: Instagram: @thecaptaincurt [https://instagram.com/thecaptaincurt] TikTok: @thecaptaincurt [https://www.tiktok.com/@thecaptaincurt] YouTube: https://www.youtube.com/@thecaptaincurt_ [https://www.youtube.com/@thecaptaincurt_] Website: www.captaincapital.com [https://www.captaincapital.com] Invest With Curt: Start Here: https://www.captaincapital.com/invest [https://www.captaincapital.com/invest] P.S. If you're enjoying the show, do us a favor—leave a review and give us a 5-star rating. It's free, takes 30 seconds, and helps us reach more listeners who need this kind of no-fluff insight.

The Woman Disrupting a $100 Billion Capital Raising Industry

What if the hardest part of real estate wasn’t finding deals — but raising the money? In this episode, Stella Han (@hellastellah) explains why traditional capital raising is fundamentally broken for small operators — and how a new model is quietly reshaping how founders, creators, and real estate investors raise capital. After losing $55,000 on her first raise, Stella built a platform designed to remove legal friction, unlock unaccredited capital, and let operators market freely — without risking jail time. What you’ll learn in this episode: * Why syndications and funds fail first-time operators * The difference between 506B, 506C, and investment clubs * How to legally market and raise capital at the same time * Why “soft commitments” without money are useless * The psychology behind requiring deposits from investors * How creators outperform traditional finance at fundraising * Why capital raising should be treated like sales * How trust and storytelling now beat spreadsheets This episode lays out the new rules of capital raising — and why operators who adapt early will have a massive edge. Timestamps 2:43 - How Stella lost $55K trying to raise $1M on her first deal 6:02 - Why 506B and 506C are broken for small operators 10:08 - Investment clubs explained: why they're not securities under SEC rules 14:20 - The hardest part of building Fractional: compliance, tech, or education? 19:39 - What surprised Stella most: operators don't build investor lists proactively 24:20 - The 3% deposit strategy that eliminates flaky verbal commitments 28:45 - Why creators raise more capital than traditional finance people 38:57 - Following up 5-6 times before an investor commits: the sales process of capital raising 43:10 - Product-market fit: 2,000 signups for a fake website that didn't exist yet 54:21 - Being a woman founder in a male-dominated space: advantage or obstacle? 1:02:56 - Is traditional capital raising outdated? Where Fractional fits in the ecosystem 1:07:27 - The Power of Habit: how mental habits shape entrepreneurial resilience CONNECT WITH STELLA HAN: Instagram: https://www.instagram.com/hellastellah/ [https://www.instagram.com/hellastellah/]   Website: https://www.fractional.app/ [https://www.fractional.app/]  CONNECT WITH US: Instagram: @thecaptaincurt [https://instagram.com/thecaptaincurt] TikTok: @thecaptaincurt [https://www.tiktok.com/@thecaptaincurt] YouTube: https://www.youtube.com/@thecaptaincurt_ [https://www.youtube.com/@thecaptaincurt_] Website: www.captaincapital.com [https://www.captaincapital.com] Invest With Curt: Start Here: https://www.captaincapital.com/invest [https://www.captaincapital.com/invest] P.S. If you're enjoying the show, do us a favor—leave a review and give us a 5-star rating. It's free, takes 30 seconds, and helps us reach more listeners who need this kind of no-fluff insight.

How to Build a $20M Real Estate Business While Keeping Your W2

What if you could build a $20 million real estate development business without quitting your W2 job?  Gaurang Gala did exactly that—working full-time as a commercial banker while raising capital, rezoning land, and developing over $92 million in assets across seven projects.  His story proves that strategic patience and understanding the math can turn dirt into generational wealth. He took a deal stuck in zoning hell for 18 months, went door-to-door in 90-degree heat wearing a suit to get neighbor signatures, turned a unanimous rejection into unanimous approval, and flipped the land for double what he paid—without ever putting a shovel in the ground. What you'll learn: * How Gaurang time-blocked his banking job into 2-3 hours a day to build his development company * Why land development creates 70% of real estate profit before the building goes vertical * The strategy behind holding land under contract for 2+ years without closing until rezoning approval * Why you should never bank at Wells Fargo, Bank of America, or Truist—and how community banks give you leverage * How to structure deals so investor money is last in, first out—and why developers take all the risk * The council member strategy: showing up in person, building relationships, and proving you're local * Why Raleigh-Durham is "the new Austin" and the Bay Area of the East Coast Gaurang isn't here to sell you a course. He's here to show you how patience, relationships, and understanding the financials can help you transition from W2 income into real estate development without betting the farm.  If you've ever wondered how to raise millions from your community, make seven figures on land deals, or build wealth through entitlements instead of construction, this episode is your roadmap. Timestamps 4:02 - Time blocking strategy: how to work a W2 and build a $20M business simultaneously 7:37 - The first deal: from 1031 exchange to 4-year rezoning nightmare 10:00 - Door-to-door in the heat: flipping zero council votes to unanimous approval 18:19 - Why you should never bank at big banks—loan-to-deposit ratio explained 22:46 - $3.5M profit on dirt: buying land, holding it 2 years, flipping it without construction 27:55 - Developer risk: why you're always first money in, last money out 34:22 - Why 70% of profit happens before vertical construction 42:06 - Raleigh-Durham: the new Austin and the Bay Area of the East Coast 47:03 - Hiring consultants who ghosted: what going door-to-door taught about doing it yourself 51:20 - What makes land development the hardest thing Gaurang has ever done 59:40 - Ray Dalio's book on empires and the debt cycle: macroeconomic concerns keeping him up at night 1:01:38 - How Gaurang wants to be remembered: great dad, community builder, giving back to immigrant kids CONNECT WITH GAURANG GALA: Instagram: https://www.instagram.com/thegrandgala/ [https://www.instagram.com/thegrandgala/] Website: https://www.galainvestments.io/ [https://www.galainvestments.io/] CONNECT WITH US: Instagram: @thecaptaincurt [https://instagram.com/thecaptaincurt] TikTok: @thecaptaincurt [https://www.tiktok.com/@thecaptaincurt] YouTube: https://www.youtube.com/@thecaptaincurt_ [https://www.youtube.com/@thecaptaincurt_] Website: www.captaincapital.com [https://www.captaincapital.com] Invest With Curt: Start Here: https://www.captaincapital.com/invest [https://www.captaincapital.com/invest] P.S. If you're enjoying the show, do us a favor—leave a review and give us a 5-star rating. It's free, takes 30 seconds, and helps us reach more listeners who need this kind of no-fluff insight.

$5 Billion in Tax Savings: The Cost Seg Strategy You're Missing

What if 70% of real estate investors are unknowingly leaving millions of dollars on the table? In this episode, Jeff Hiatt, founder of MSC Cost Segregation Consultants, breaks down how cost segregation has helped over 26,000 clients save more than $5 billion — using strategies that have existed in the tax code since 1986. This conversation goes far beyond theory and into how serious investors actually use tax strategy to scale faster. What you’ll learn in this episode: * Why 70% of investors should be doing cost segregation — and aren’t * How accelerated depreciation increases the velocity of capital * The difference between straight-line depreciation and cost segregation * How investors can retroactively claim deductions without amending returns * Why cutting corners with cheap studies can trigger painful audits * How cost segregation fits into 1031 exchanges and long-term planning * Why taxes should be treated as a strategy, not an afterthought If you’re serious about scaling real estate, this episode shows why tax strategy isn’t optional, it’s foundational. Timestamps 3:07 - Would you rather take a deduction now or wait 27.5 years for the same one? 4:34 - Why 70% of investors who should do cost seg never do it 6:10 - How one $4M tax savings changed Jeff's business overnight 10:42 - Real example: $1M property, $800K basis—how much can you write off year one? 16:36 - Big Beautiful Bill brings back 100% bonus depreciation—what investors need to know 18:33 - Going back to 1986: grabbing retroactive deductions without amending returns 20:23 - The Iron Silo: tracking components for abandonment losses during renovations 30:10 - Short-term rental loophole: how W2 earners offset income with rental losses 32:49 - Recapture explained: what you owe when you sell and how 1031s defer it forever 35:57 - Why $500 online tools and remote studies fail IRS audits 41:07 - Which asset classes give the highest cost seg results (hotels vs industrial) 56:27 - When to engage cost seg services: before purchase, during construction, or retroactively CONNECT WITH JEFF HIATT: Instagram: https://www.instagram.com/depreciationdoctor/ [https://www.instagram.com/depreciationdoctor/]   Website: https://msc.tax/ [https://msc.tax/] CONNECT WITH US: Instagram: @thecaptaincurt [https://instagram.com/thecaptaincurt] TikTok: @thecaptaincurt [https://www.tiktok.com/@thecaptaincurt] YouTube: https://www.youtube.com/@thecaptaincurt_ [https://www.youtube.com/@thecaptaincurt_] Website: www.captaincapital.com [https://www.captaincapital.com] Invest With Curt: Start Here: https://www.captaincapital.com/invest [https://www.captaincapital.com/invest] P.S. If you're enjoying the show, do us a favor—leave a review and give us a 5-star rating. It's free, takes 30 seconds, and helps us reach more listeners who need this kind of no-fluff insight.

From $30K Monthly to Zero: The Injury That Changed Everything

What if one real estate deal paid you more than 20 years in your profession? In this episode, Wayde Elliott, founder of Store It, shares how a career-ending injury forced him to walk away from dentistry — and how a series of failures eventually led him to build a self-storage portfolio worth over $50 million. This conversation dives deep into beliefs, risk, and what it really takes to pivot into real estate later in life. What you’ll learn in this episode: * The moment Wayde lost his dental career overnight * Why trading time for money became unacceptable * The costly business failures that shaped his investing philosophy * How his first self-storage deal rewired his beliefs around money * Why self storage performs in both good and bad economies * How values and partnerships can make or break long-term success * The belief system that allowed him to go all-in on development This is a powerful reminder that the right pivot — at the right moment — can completely change the trajectory of your life and wealth. Timestamps 3:08 - Going from $30K monthly dental income to zero: the fear and the blessing 4:21 - The patient who planted the seed: six storage facilities and total freedom 6:06 - Growth mindset vs scarcity mindset: always seeking the uncomfortable 10:11 - Faith vs fear: both demand you believe in something you cannot see 16:37 - The three T's of investing: trust, transparency, and track record 20:42 - The belief cycle: how money stories from childhood shape your wealth 30:15 - Losing $800K in cannabis but refusing to quit 31:48 - The development PhD: wetlands, flooding, railroad negotiations, and moving highways 34:25 - When to cut ties with partners not aligned on values 37:01 - Why self storage is recession-resilient in both good and bad economies 41:39 - Finding deals: looking for baked-in value from day one 46:36 - 600+ five-star reviews: why exceptional customer service wins in storage 51:34 - The ayahuasca journey that changed Wade and his son's life CONNECT WITH WAYDE ELLIOTT: Instagram: https://www.instagram.com/waydeelliottdmd [https://www.instagram.com/waydeelliottdmd]   Website: https://www.storeit.com/ [https://www.storeit.com/] CONNECT WITH US: Instagram: @thecaptaincurt [https://instagram.com/thecaptaincurt] TikTok: @thecaptaincurt [https://www.tiktok.com/@thecaptaincurt] YouTube: https://www.youtube.com/@thecaptaincurt_ [https://www.youtube.com/@thecaptaincurt_] Website: www.captaincapital.com [https://www.captaincapital.com] Invest With Curt: Start Here: https://www.captaincapital.com/invest [https://www.captaincapital.com/invest] P.S. If you're enjoying the show, do us a favor—leave a review and give us a 5-star rating. It's free, takes 30 seconds, and helps us reach more listeners who need this kind of no-fluff insight.